Trifluoroacetic acid → HCID 69128036, compound

HRID 2064197Notes

Reaction equation

HRID 2064197 reaction equation
[C:1]([C:3]1[C:25]([CH3:26])=[CH:24][C:6]2[N:7]([CH:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[C:8](=[O:10])[NH:9][C:5]=2[CH:4]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[CH3:26][C:25]1[C:3]([C:1]#[N:2])=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[C:6]=2[CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69127458HCID 69127458, compound

Product 1

HCID 69128036HCID 69128036, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl 4-(5-cyano-6-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate (D93) (2.6 mmol, 1.15 g crude material) in dichloromethane (3 mL) was treated with trifluoroacetic acid (3 mL) under argon at room temperature and was allowed to stir for 1 h. The mixture was then concentrated under reduced pressure, the residue was treated with 10% aqueous sodium carbonate solution and extracted 3 times with ethyl acetate. The organics were combined, dried and concentrated under reduced pressure to give the title compound (2.66 mmol, 680 mg, ˜100%). M+H 257.2.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. additionthe residue was treated with 10% aqueous sodium carbonate solution
  3. extractionextracted 3 times with ethyl acetate
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0692fe8ef7647aaaee6b9b6269f285f
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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